


Gamble

by doctor__idiot



Category: Gilmore Girls
Genre: First Time, Hand Jobs, M/M
Language: English
Status: Completed
Published: 2015-05-24
Updated: 2015-05-24
Packaged: 2018-04-01 01:19:04
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,985
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4000513
Author URL: https://archiveofourown.org/users/doctor__idiot/pseuds/doctor__idiot
Summary: <blockquote class="userstuff">
              <p>Jess was staring up at him and it wasn’t the first time Dean noticed how dark his lashes were. It was, however, the first time he noticed how delicate his nose was and how plush his lips. Granted, right now there were pulled taut in anger, but they were still pretty.</p>
            </blockquote>





	Gamble

**Author's Note:**

> I have no excuse for this. Except that I've been re-watching the show and I was half-way through season 3 when I couldn't stand the UST anymore.  
> I'm not sure about the timeline for this. You make something up.
> 
> Disclaimer: Only the idea is mine. Unbeta'd - there may be mistakes because I was pretty tired when I wrote this. (On second thought, that probably explains a lot.)

“Oh, you’re doing that looming thing again. You realize it’s getting old?" 

Dean wasn’t sure what he was doing here but since he _was_ here, he might as well go through with it.

Jess was staring up at him and it wasn’t the first time Dean noticed how dark his lashes were. It was, however, the first time he noticed how delicate his nose was and how plush his lips. Granted, right now there were pulled taut in anger, but they were still pretty.

It was the first time Dean noticed how Jess turned into him, even though his words were snide and his features grim. How his body responded, possibly without him realizing.

Dean moved. He took hold of Jess’s wrists, fingers able to wrap around them fully, pushed him against the side of the gazebo and it would have been too public a place hadn’t it been 10:30 at night. 

The sound Jess made was surprised and broken and they were both taken aback by it. Jess flexed his wrists, testing the grip, and the grind of bone and sinew against the palms of Dean’s hands almost made him think, _fragile_.

But that wasn’t true. Dean could have made a crack about Jess’s height and his soft features that appeared harder with experience, could probably have lifted him up without much of an effort, but what he felt against his chest, his legs, was solid muscle. 

It was disconcerting how much of a difference that made. 

“I notice you’re not running away.”

Jess exhaled in a hiss, lips curling sardonically, “I notice you’re being a pussy.”

It was unexpected and it was a challenge and Dean took it without thinking about it. Their mouths crashed into each other, Jess’s head knocked back against the gazebo wall and he bit down on Dean’s lip, accidentally or on purpose, nobody could say for sure.

It was much closer to a fight than a kiss. It wasn’t particularly coordinated or passionate, it was mainly desperate.

Dean couldn’t for the life of him say how it had spiraled out of control so easily. All he had known before tonight was that Jess riled him up like no other and he seemed to take great pleasure in it. Admittedly, he was a jerk to everyone but Rory but maybe Jess had fixed onto Dean as much Dean had onto him.

Dean had thought it was jealousy, protectiveness, and possessiveness in its ugliest form. And it probably was, only the question now was whom he was jealous of. Whom he wanted to possess and protect.

He wasn’t in love with Jess, not in the common sense of the phrase. Jess fascinated him and his reaction to the way Jess was fitting himself against him made his head swim. 

He let go of Jess’s wrists to wrap an arm around him, dragging them closer together and, to his surprise, Jess reached up, knuckles brushing his cheekbones, and knotted his fingers in Dean’s hair.

 _What are we doing_ , Dean wanted to ask but didn’t. For one, his mouth was busy, two, he wasn’t sure he wanted to know the answer. He would never admit it but he was afraid either one of them would come to their senses and this would be over before it had begun. 

Dean didn’t know what _this_ was but he knew he didn’t want it to be over yet.

He gathered Jess more tightly against him, arms around him, and it was scary how good it was to feel all those hard planes, sharp bones, and tense muscles beneath his fingertips. It was even scarier how Jess’s hands on him seemed to leave fire in their wake, trailing over his back, fingertips dipping between his shoulder blades, searing invisible marks into his skin through his T-shirt.

Dean’s fingers dug into Jess’s sides and Jess moaned into his mouth. It was probably an involuntary sound but he didn’t seem to be embarrassed by it and Dean lapped it right up, licked it out of Jess’s mouth, their teeth occasionally clicking against each other because they couldn’t care less about finesse.

Dean pulled away at last, breathing hard, and the night was dark but Jess’s eyes were darker and he was looking at Dean with a smirk in the corner of his mouth, half-way between cruel and fond, and Dean felt want zing through him. 

He had never wanted anyone as he wanted Jess right now and he genuinely wondered how that had managed to creep up on him.

It probably didn’t matter because Jess looked equally unsure, eyes flicking down and up, and his nails were biting into a spot below Dean’s ear, making him shiver. He wanted to blame it on the temperature outside.

“Luke’s at Lorelai’s.” It rushed out of Jess all in one breath and that he was speaking at all took a few seconds to register with Dean.

“So?” he asked dumbly until the haze had cleared from his brain a little. “Oh.”

Did he even want that? Had someone asked him that a minute ago when he had had his tongue in Jess’s mouth and Jess’s hands on him, he wouldn’t have hesitated. Now, that the night chilled him and he had brought some distance between them, it trickled into his brain how bad of an idea any of this was.

But Jess was looking at him with both a dare and a plea in his eyes and he couldn’t think about anything else than getting his teeth on that jawline, that neck, his mouth onto those abs, around that cock.

“Lead the way,” he said huskily and made a gesture with his hand. Jess glanced at him from under his lashes, playing all the right cards. He twisted his fingers in Dean’s shirt, tugged him along.

Dean hadn’t ever been in Luke’s apartment and before it could occur to him how inappropriate any of it was, Jess’s hands had snuck under his clothes, palms splaying against his stomach, and he could only just hold back a moan. 

He hadn’t thought he would ever say this or even just think it, but everything about Jess was addicting. The way he smelled, like smoke and ink and hair gel, the way his hair felt as it curled around the tips of Dean’s fingers. The hard line of his body, his mouth, _goddammit_ , his mouth. 

Dean nipped his lower lip, tugging it into his mouth and sucking, licking at a little drop of blood where teeth had caught delicate skin, and Jess hissed, pulled him closer.

Their height difference made it somewhat challenging but they fit together strangely well and Dean was long used to the crick in his neck that he lived with. 

Then they found their way into the kitchen and Jess, clever Jess, pulled himself up onto the counter top, bracketing Dean’s hips with his legs and they were on eye-level now.

It was easier to kiss down Jess’s neck this way, so that’s what Dean did. He let his teeth catch here and there, not shying away from sucking small marks into the skin and Jess didn’t complain, just clutched at him, arm around his shoulder, hand in his hair. He didn’t so much guide Dean as hold on to him and Dean slowly peeled Jess’s shirt away from his collar bone. 

He bit down on the sinewy part between Jess’s neck and shoulder and when Jess jerked against him, he noticed for the first time with distinctive clarity that they were both rock-hard in their jeans.

“You sure you wanna do this?” someone asked and Dean realized that it was him.

Jess looked at him, sucked his lower lip into his mouth. Distracting. “No. Yes. Probably.”

Dean was glad to see they were on the same page with their confusion. “Yeah. We just won’t tell anyone.”

“Works for me.”

Tangled up as they were, it wasn’t the easiest feat to shuck their clothes, but they somehow managed. Dean dragged their hips together, moans muffled between their mouths, while Jess closed his hand around the both of them to the best of his abilities.

They were rutting together without much finesse but it was working, cocks coated with precome, and Dean lend another hand, twining his fingers with Jess’s. 

They thrust together that way until Dean felt Jess’s muscles tense up and he stroked them both faster, kissed him harder, made room for himself in more than just Jess’s arms or between his legs.

Orgasms hit nearly simultaneously and they kept stroking until it was almost painful, not letting go off each other before they had their breath break.

Jess opened his eyes, blinked at Dean as if he was only now realizing where he was, and Dean felt raw, too vulnerable for his own comfort because this was Jess with the sharp tongue and rough hands, able to destroy with only so much as his words.

He wasn’t saying anything now and that was more cause for concern than anything else. His throat worked, possibly _wanting_ to say something but not trusting his own voice.

Dean stepped back to let Jess slide off the counter, instinctively steadying him when he stumbled slightly. To Dean’s surprise, Jess didn’t twist away or pushed him, just muttered, “Thanks,” and didn’t take his eyes off the floor.

It was a crushing silence while they dressed, perfunctorily wiping themselves down with paper towels. It was a nearly comical shuffle of not getting into each other’s way, always keeping at least a foot distance between them.

On Jess’s way to the door, Dean had had enough. He grabbed for Jess’s wrist, felt his pulse jump under his fingertips.

“What?” It didn’t sound as aggressive as Jess probably would have liked, voice slightly hoarse.

“We’re gonna run into each other eventually and I really don’t want it to be awkward.”

Dean might have expected Jess to give lip, sweeping the blame over to Dean and making him the bad guy in all of this. Which, Dean supposed, wouldn’t have been entirely unfair.

Jess didn’t, however. Just sighed, “We don’t have to talk to each other. ’S not like we’ve been best friends all this time.”

“I know.”

What Dean didn’t know was why that suddenly bothered him. Not the best-friends part. The not-talking part.

Jess finally looked up at him, wrist still in the circle of Dean’s fingers. He didn’t make a move to escape. “So?”

Dean let him go, combed his hand through his hair to conceal the light tremor. “No, you’re right.” 

He was way out of his depth here. They didn’t even like each other. They wouldn’t last five minutes in a room together if they actually had to talk to each other. 

Well, Dean thought, they had sidestepped _that_ well tonight. 

He noticed Jess hadn’t made another attempt at running for the door. He was still looking at Dean, expression unreadable. But then again, none of Jess’s expressions were particularly telling.

Dean suddenly found himself wanting to know each and every single one of them, learning what they mean and how to react to them. He found himself wanting to knock down some of those barriers that Jess had been building all his life. Strip him bare in the figurative sense, just as he had done in the literal.

There was still that phantom sensation of Jess’s smooth skin under his hands, the ghost of the hint of stubble rubbing against Dean’s chin. He shook himself out of it. 

Jess still hadn’t moved. He seemed to be waiting for something, anticipating.

Belatedly Dean realized what he was waiting for and he hoped his cheeks didn’t flush as hot red as they felt. He cleared his throat, lamely said the first thing that came to mind, “Do you … maybe wanna watch a movie sometime?”

For the first time that evening, Jess smiled.


End file.
